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Cheap flights from Chicago O'Hare Intl Airport to Caribbean from $68

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Caribbean departing on 12/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Caribbean

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago O'Hare Intl Airport to Caribbean that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago O'Hare Intl Airport to Caribbean.

Cheap last minute flights

Planning a quick getaway from Chicago O'Hare Intl Airport to Caribbean? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Caribbean, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago O'Hare Intl Airport to Caribbean

Find recent round-trip train or bus tickets from Chicago O'Hare Intl Airport to Caribbean.

All round-trip flight deals to Caribbean

The cheapest plane tickets to Caribbean found on KAYAK recently.
8:32 am - 3:05 pmORD-SJU
4h 33mnonstop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$126Spirit Airlines
Find Deal
Tue, Dec 3 - Wed, Dec 11
5:56 pm - 12:05 pmORD-SJU
16h 09m1 stop
10:47 pm - 9:08 amSJU-ORD
12h 21m1 stop
$132Frontier
Find Deal
Fri, Feb 21 - Mon, Feb 24
10:43 am - 5:11 pmORD-PUJ
4h 28mnonstop
5:25 pm - 11:20 pmPUJ-ORD
7h 55m1 stop
$339United Airlines
Find Deal
Mon, Dec 9 - Mon, Dec 16
5:00 am - 5:00 pmORD-PUJ
10h 00m1 stop
6:00 pm - 8:48 amPUJ-ORD
16h 48m1 stop
$343American Airlines
Find Deal
Sun, Dec 8 - Wed, Dec 11
6:52 am - 5:00 pmORD-PUJ
8h 08m1 stop
2:21 pm - 8:04 pmPUJ-ORD
7h 43m1 stop
$353American Airlines
Find Deal
Fri, Dec 6 - Fri, Dec 13
7:10 am - 4:40 pmORD-PUJ
7h 30m1 stop
3:44 pm - 9:15 pmPUJ-ORD
7h 31m1 stop
$368Delta
Find Deal
Tue, Nov 12 - Wed, Nov 20
8:56 am - 4:55 pmORD-NAS
6h 59m1 stop
11:50 am - 10:46 pmNAS-ORD
11h 56m1 stop
$369JetBlue
Find Deal
Sat, Nov 16 - Sat, Nov 23
7:10 am - 4:40 pmORD-PUJ
7h 30m1 stop
6:05 pm - 11:59 pmPUJ-ORD
7h 54m1 stop
$373Delta
Find Deal
Sun, Nov 17 - Mon, Nov 25
10:43 am - 5:11 pmORD-PUJ
4h 28mnonstop
5:25 pm - 11:20 pmPUJ-ORD
7h 55m1 stop
$394United Airlines
Find Deal
Mon, Nov 4 - Sat, Nov 23
9:48 am - 4:55 pmORD-NAS
6h 07m1 stop
11:50 am - 10:46 pmNAS-ORD
11h 56m1 stop
$399JetBlue
Find Deal
Mon, Nov 18 - Sat, Nov 23
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$68Spirit Airlines
Find Deal
Tue, Dec 10
4:58 pm - 2:02 amORD-SJU
7h 04m1 stop
$69Frontier
Find Deal
Mon, Dec 9
8:51 am - 7:19 pmORD-SJU
8h 28m1 stop
$143JetBlue
Find Deal
Sat, Dec 7
9:48 am - 4:55 pmORD-NAS
6h 07m1 stop
$146JetBlue
Find Deal
Mon, Nov 18
4:28 pm - 11:50 amORD-PUJ
17h 22m1 stop
$160American Airlines
Find Deal
Mon, Dec 9
6:20 am - 4:52 pmORD-PUJ
8h 32m1 stop
$165Delta
Find Deal
Wed, Jan 1
10:43 am - 5:11 pmORD-PUJ
4h 28mnonstop
$176United Airlines
Find Deal
Mon, Nov 11
8:20 am - 2:00 pmORD-SJU
4h 40mnonstop
$183American Airlines
Find Deal
Sun, Mar 9
2:05 pm - 12:19 amORD-SJU
8h 14m1 stop
$202Delta
Find Deal
Tue, Nov 5
8:41 am - 1:46 pmORD-MBJ
4h 05mnonstop
$207United Airlines
Find Deal
Tue, Jan 21
10:16 am - 3:40 amORD-SJU
15h 24m1 stop
3:59 am - 5:41 pmSJU-ORD
15h 42m1 stop
Mon, Nov 4 - Fri, Nov 15
10:16 am - 2:39 amORD-SJU
14h 23m1 stop
3:59 am - 12:05 pmSJU-ORD
10h 06m1 stop
Mon, Nov 4 - Tue, Nov 12
10:16 am - 2:39 amORD-SJU
14h 23m1 stop
9:44 pm - 1:13 amSJU-ORD
5h 29mnonstop
$248Spirit Airlines
Find Deal
Mon, Nov 4 - Thu, Nov 14
4:19 pm - 2:55 amORD-SJU
8h 36m1 stop
3:59 am - 12:05 pmSJU-ORD
10h 06m1 stop
$258Frontier
Find Deal
Mon, Nov 4 - Tue, Nov 12
10:16 am - 2:39 amORD-SJU
14h 23m1 stop
8:17 pm - 6:49 pmSJU-ORD
24h 32m2 stops
$263Spirit Airlines
Find Deal
Sun, Nov 3 - Wed, Nov 6
8:39 pm - 1:55 amORD-SJU
28h 16m1 stop
10:35 am - 7:18 pmSJU-ORD
10h 43m1 stop
$274Frontier
Find Deal
Fri, Nov 1 - Fri, Nov 15
7:40 am - 1:08 pmORD-PUJ
4h 28mnonstop
5:25 pm - 11:20 pmPUJ-ORD
7h 55m1 stop
$384United Airlines
Find Deal
Sat, Nov 2 - Fri, Nov 22
8:50 am - 4:35 pmORD-PUJ
6h 45m1 stop
1:00 pm - 11:20 pmPUJ-ORD
12h 20m1 stop
$388United Airlines
Find Deal
Sat, Nov 2 - Fri, Nov 22
7:45 pm - 11:49 amORD-PUJ
15h 04m1 stop
3:37 pm - 6:52 pmPUJ-ORD
5h 15mnonstop
$398American Airlines
Find Deal
Sat, Nov 2 - Wed, Nov 6
7:45 pm - 11:50 amORD-SJU
15h 05m1 stop
5:50 am - 2:10 pmSJU-ORD
10h 20m2 stops
$399American Airlines
Find Deal
Sat, Nov 2 - Sat, Nov 16
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$157Spirit Airlines
Find Deal
Wed, Dec 11 - Tue, Jan 14
8:32 am - 3:05 pmORD-SJU
4h 33mnonstop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$158Spirit Airlines
Find Deal
Tue, Dec 3 - Wed, Dec 11
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$173Spirit Airlines
Find Deal
Wed, Dec 11 - Wed, Feb 5
6:00 am - 12:29 pmORD-PUJ
4h 29mnonstop
5:00 pm - 8:31 pmPUJ-ORD
5h 31mnonstop
$189Frontier
Find Deal
Mon, Dec 9 - Fri, Dec 13
6:00 am - 12:29 pmORD-PUJ
4h 29mnonstop
5:00 pm - 8:31 pmPUJ-ORD
5h 31mnonstop
$200Frontier
Find Deal
Mon, Dec 9 - Wed, Dec 11
8:20 am - 2:00 pmORD-SJU
4h 40mnonstop
3:15 pm - 7:40 pmSJU-ORD
5h 25mnonstop
$365American Airlines
Find Deal
Sun, Mar 9 - Thu, Mar 13
8:12 am - 2:37 pmORD-PUJ
4h 25mnonstop
3:37 pm - 6:52 pmPUJ-ORD
5h 15mnonstop
$384American Airlines
Find Deal
Sat, Nov 16 - Wed, Nov 20
10:43 am - 5:11 pmORD-PUJ
4h 28mnonstop
2:50 pm - 6:00 pmPUJ-ORD
5h 10mnonstop
$405United Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 22
10:43 am - 5:11 pmORD-PUJ
4h 28mnonstop
2:50 pm - 6:00 pmPUJ-ORD
5h 10mnonstop
$435United Airlines
Find Deal
Fri, Nov 15 - Wed, Nov 20
8:52 am - 4:25 pmORD-UVF
5h 33mnonstop
1:52 pm - 6:15 pmUVF-ORD
6h 23mnonstop
$1,036Lufthansa
Find Deal
Sat, Feb 15 - Sat, Mar 1

Frontier flights from Chicago O'Hare Intl Airport to Caribbean

Our best Frontier deals on Chicago O'Hare Intl Airport to Caribbean flight tickets
Frontier
Feb 21
ORD5:56 pmChicago O'Hare Intl
16h 09m
1 stop
SJU12:05 pmSan Juan Luis Munoz Marin Intl
Feb 24
SJU10:47 pmSan Juan Luis Munoz Marin Intl
12h 21m
1 stop
ORD9:08 amChicago O'Hare Intl
Frontier
Dec 9
ORD4:58 pmChicago O'Hare Intl
7h 04m
1 stop
SJU2:02 amSan Juan Luis Munoz Marin Intl
Dec 13
SJU1:55 pmSan Juan Luis Munoz Marin Intl
11h 52m
1 stop
ORD11:47 pmChicago O'Hare Intl
Frontier
Jan 6
ORD4:41 pmChicago O'Hare Intl
11h 49m
1 stop
SJU6:30 amSan Juan Luis Munoz Marin Intl
Jan 15
SJU4:49 pmSan Juan Luis Munoz Marin Intl
22h 54m
1 stop
ORD1:43 pmChicago O'Hare Intl

Spirit Airlines flights from Chicago O'Hare Intl Airport to Caribbean

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Caribbean flight tickets
Spirit Airlines
Dec 3
ORD8:32 amChicago O'Hare Intl
4h 33m
SJU3:05 pmSan Juan Luis Munoz Marin Intl
Dec 11
SJU2:17 pmSan Juan Luis Munoz Marin Intl
5h 30m
ORD5:47 pmChicago O'Hare Intl
Spirit Airlines
Dec 3
ORD6:11 pmChicago O'Hare Intl
4h 32m
SJU12:43 amSan Juan Luis Munoz Marin Intl
Dec 11
SJU2:17 pmSan Juan Luis Munoz Marin Intl
5h 30m
ORD5:47 pmChicago O'Hare Intl
Spirit Airlines
Dec 3
ORD9:10 pmChicago O'Hare Intl
12h 51m
1 stop
SJU12:01 pmSan Juan Luis Munoz Marin Intl
Dec 11
SJU2:17 pmSan Juan Luis Munoz Marin Intl
5h 30m
ORD5:47 pmChicago O'Hare Intl

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Caribbean

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies to Caribbean from Chicago O'Hare Intl Airport?

Frontier. Frontier, Spirit Airlines, and Copa Airlines are the most popular carriers operating from Chicago O'Hare Intl Airport to Caribbean

What cabin class options are available on Chicago O'Hare Intl Airport to Caribbean flights?

There are 2 cabin classes available to choose from on Chicago O'Hare Intl Airport to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago O'Hare Intl Airport to Caribbean flights?

You could potentially save up to 16% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Caribbean flight.

Cheap Chicago O'Hare Intl Airport to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Caribbean

Best Price Found

$68

Fastest flight time

3h 21m

Direct flights

Every day

Airports in Caribbean

6 airports
The best one-way flight to Caribbean from Chicago O'Hare Intl Airport in the past 72 hours is $68. The best round-trip flight deal from Chicago O'Hare Intl Airport to Caribbean found on momondo in the last 72 hours is $126.
The fastest flight from Chicago O'Hare Intl Airport to Caribbean takes 3h 21m
Direct flights go from Chicago O'Hare Intl Airport to Caribbean every day.
There are 6 airports near Caribbean: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Caribbean?

    Prices for flights from Chicago O'Hare Intl Airport to Caribbean refresh daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Caribbean?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Caribbean?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Caribbean.

  • What documentation or ID do you need to fly to Caribbean?

    The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Caribbean?


Best airlines flying from Chicago O'Hare Intl Airport to Caribbean

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Caribbean with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $117Free CancellationRating
6.1
3,580 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $159Free CancellationRating
6.3
8,190 reviews
Search Spirit Airlines flights
JetBluePriceFrom $173Free CancellationRating
7.5
3,514 reviews
Search JetBlue flights
DeltaPriceFrom $204Free CancellationRating
8.0
8,835 reviews
Search Delta flights
United AirlinesPriceFrom $268Free CancellationRating
7.4
9,240 reviews
Search United Airlines flights
American AirlinesPriceFrom $325Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Copa AirlinesPriceFrom $379Free CancellationRating
7.7
1,885 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $526Free CancellationRating
7.0
8,095 reviews
Search Air Canada flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Caribbean?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Caribbean for you.

Can I find flights from Chicago to Caribbean with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean from Chicago with this policy.

How can momondo help me find flights from Chicago to Caribbean?

Once all potential Chicago to Caribbean flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Caribbean right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Caribbean, momondo offers a useful price alert feature which will track prices for flights to Caribbean from Chicago and alert you when they change.


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